Pegged and Denied: His Longest Night Ever

There is a special kind of cruelty that isn't cruel at all, and it is called getting pegged and denied. I discovered my talent for it on a weekend getaway with my boyfriend, in a hotel room with a minibar and a lock on the door, and he still talks about that night in a hushed voice like it was a religious experience. Honestly? It kind of was. For both of us.

We had driven out to the coast for a long weekend, just us, no plans except room service and each other. On the drive up, he got quiet in that way he gets when he wants something but is working up the nerve to ask. Finally, at a rest stop somewhere, he said he had a request for the trip. He wanted me to peg him again, like the first time, but this time he wanted me to be, in his words, meaner about it. I laughed so hard I snorted, and I told him that for him, I would be the meanest brat on the entire coastline.

I had packed accordingly, because I always pack accordingly. That first night, after dinner and a bottle of wine, I laid out my plan while he sat on the edge of the hotel bed looking increasingly nervous. The rules were simple. Tonight, I was going to peg him until he couldn't think straight. And he was not going to come. Not once. If he could make it through the night without finishing, there would be a reward in the morning. If he finished without permission, the reward would vanish, and so would my mercy.

He agreed immediately, which was his first mistake, because he had no idea what he was agreeing to.

I started slow and sweet, which was deliberate. Lots of prep, lots of praise, me telling him how good he was taking it, lulling him into a false sense of security. Then, once he was relaxed and moaning and completely under my spell, I changed gears. I set a rhythm that was deep and relentless and perfect, the exact pace I knew drove him wild, and I watched his body start to climb. His breathing went ragged. His hands fisted the hotel sheets. And right when he was at the very edge, making that desperate sound I know so well, I stopped. Completely. Pulled back and just looked at him, all flushed and wrecked and throbbing.

The look on his face was priceless. Betrayal, disbelief, and underneath it all, the most intense arousal I had ever seen on him. I told him, very sweetly, that I had said no coming, and he had agreed, and good boys keep their agreements. He nodded, dazed, and I started again.

I did it four times that night. Four perfect climbs to the edge, four exquisite denials. Each time I varied it: once slow and deep, once fast and hard, once with my hand wrapped tight around him but never quite enough, once with me whispering filthy promises about the morning reward. By the fourth denial he was actually crying, tears on his cheeks, begging me in this broken voice to either let him finish or stop entirely because he couldn't take it anymore. I kissed his tears away and told him he was doing so beautifully, and then I kept going, because I am a brat and his suffering was the most beautiful thing I had ever seen.

When I finally decided he had suffered enough, I didn't let him come. That was the twist he never saw coming. I slid off him, all cool and satisfied, and pulled out the little lock I had packed. I told him the night was over, he had been magnificent, and now he was going to stay exactly like this, denied and aching, until morning. He stared at me like I had lost my mind. I locked him up, tucked him in like a good boy, and fell asleep listening to him squirm.

Morning came, and I woke up to find him watching me with the most intense eyes I have ever seen. I made him beg for his reward over breakfast, in the hotel restaurant, in public, whispering. Then I took him back upstairs and finally, finally let him finish, and it was the most explosive release either of us had ever witnessed. He shook for minutes. He laughed and cried at the same time. Then he looked at me and said it was the best night of his life, which is funny, because he spent most of it not coming.

He still asks for denial nights. I ration them carefully, because a brat knows that the best treats are the ones you have to wait for. And every time he begs, I just smile and check my schedule. Maybe next weekend. Maybe.